Sulfuric Acid → 2-Chloro-2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanol

HRID 1589413Notes

Reaction equation

HRID 1589413 reaction equation
[CH3:1][O:2][C:3]([O:6][CH3:7])([CH3:5])[CH3:4].[Cl:8][CH:9](CO)[CH:10]([OH:13])CO.S(=O)(=O)(O)O.[OH-].[Ba+2].[OH-]>CC(C)=O.O>[Cl:8][CH:9]([CH:1]1[CH2:7][O:6][C:3]([CH3:5])([CH3:4])[O:2]1)[CH2:10][OH:13]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 64952,2-DimethoxypropaneHCID 6093286Barium hydroxideHCID 106068313-Chlorobutane-1,2,4-triol

Product 1

HCID 131868262-Chloro-2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanol

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Within 2 hours, 258 ml of 2,2-dimethoxypropane is added dropwise to a stirred and water-cooled solution of 272 g of 3-chloro-1,2,4-butanetriol and 0.5 ml of concentrated sulfuric acid in 1 liter of acetone. The reaction is completed after another 4 hours. The solution is neutralized by the addition of 3.8 g of barium hydroxide, stirred for 30 minutes, filtered off from the solid matter, and concentrated to dryness under vacuum, yielding 2-chloro-2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanol as a yellow oil.

Workup

  1. waitThe reaction is completed after another 4 hours
  2. stirringstirred for 30 minutes
  3. filtrationfiltered off from the solid matter
  4. concentrationconcentrated to dryness under vacuum

Sources & evidence

ORD record
ord-3ac5c7daa01d4fc290b56757b8ab3d0a
Source dataset
uspto-grants-1986_02
Patent number
US04570007

Reaction notes

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